Britney's Errand Boy

This story is completely fictional and I hope you enjoy it. Feel free to send any comments or suggestions.

I just put on my brand new yellow Staff Event T-shirt getting ready to go to work. I looked up at my wall and started to count. This was my 10th T-shirt since I started my job. You see, I work as an "Errand Boy" for musicians when they perform here at the Verizon Wireless Music Center (formerly known as Deer Creek). After I fetch whatever the stars want they usually ask how they could repay me (I make it my duty to get the item to the person in as little time as possible, which have also led to one or two speeding tickets). I would usually have the person or the entire band sign my shirt and take a picture with me, I would then go straight home after the concert and put both items in a picture frame and hang it on my wall.

But tonight was a different story. Tonight I was supposed to work the Britney Spears concert and I wasn't looking forward to it. Of course when her music first came out I loved it, but then, I don't know it just didn't sound right anymore. It was like she was doing it for the money instead of the fans. I went into the bathroom and combed my short blonde hair and admired my brown eyes for a second. Even though girls admired me from afar, I still didn't have a girlfriend. I put my small-framed glasses on and hopped into my car and was gone.

At first when I took this job, it was to save money for college to get a career in Electronics, but since I started my collection of autographed shirts I've only had money for the bare essentials. Minutes later I arrived at work and checked in with my boss. I came in with a cheesy smile and he said to me, "Here Travis." He said and tossed me another shirt.

"Thanks boss. But I doubt I'll need it for this one. My collection includes musicians that I like." I replied.

"Yeah, but I bet you could make some serious money with her autograph."

I smiled and said, "Yeah I may get her autograph and then get the hell out of here. So, what kind of mood is she in."

My boss shrugged. "Okay but I hear that she yells at Errand Boys who fuck up her orders."

I sighed. "Okay. Just call my parents if I fuck up to much and have them plan the funeral. My boss and I smiled and I said, "Well, I'm off to see what the ‘Pop Princess' is in need of." He gave me a wave and I was off.

I found her dressing room and knocked on the door. "Ms. Spears." I hollered into the door. The door opened and there was Britney with only a towel wrapped around her body. "Hello Ms. Spears. I'm Travis the Errand Boy. I'm here to pick up your list of requested items."

She smiled and handed the list to me. "Just call me Britney."

I took a quick look over the list, it mainly had junk food written all over it. I smiled back at her and said, "This is one of the easiest lists I've had in a while. It shouldn't take me no more than 15 minutes."

She still held her smile and said, "Okay. No rush at all." I left out into the parking lot and hopped into my car and went to a nearby Wal-Mart and grabbed her stuff and wouldn't you know it, there were only two lanes open so it took me nearly thirty minutes. I finally I got out of there and back to the stadium.

While walking through the halls I saw my friend Mark. Mark works for security. "Hey Mark." I said.

He smiled and said, "What's up Travis?"

"Trying to get this stuff to Britney before she goes on." I replied.

He started to chuckle to himself. "You're about 10 minutes late for that."

"What do you mean?" I asked.

"She just went on stage. Didn't you hear the music?"

I pulled my headphones off. Now blaring "Beautiful" by Creed. "Oh fuck. My ass is gonna be in a sling now." I rushed past Mark and hollered, "Later." He was still laughing when hollered his "later" to me. When I arrived to her door, there was a note taped to the door. "Errand Boy, wait inside for me. Help yourself to whatever's in the cooler."

I went inside and set her things down and grabbed a Pepsi from her cooler. I sat down and about an hour or so later, the door opened and in walked Britney sweating rather badly. The first thing I did was grab a towel and walked up to her and handed her the towel.

"Thanks." She said, taking the towel and wiping the sweat off her body. "So what happened to you?" She asked, with a slight hint of concern in her voice.

"They only had two lanes opened at the damn Wal-Mart and about 30 people in each line. But I did get everything on the list." I picked the bag up and handed it to her. She flashed me her flawless smile. God, what a smile, even though I wasn't a big fan of her music, she was still a very beautiful lady.

"So how much do I owe you?" She asked.

"Only five dollars." I replied.

She looked in the bag again. This here is the biggest quantities of these items, and it only cost five bucks?"

"Well actually," I started, "it's more like 25 bucks, but I paid for 20 of it myself. Anytime I have to pick up any item, I pay a maximum of 20 dollars out of my own pocket and then my boss or the performers themselves pay me the difference

..

"Oh." Britney said, "Well, here's ten for your trouble."

I took the money and said, "Thanks Britney." I started to leave when I stopped. "Britney, may I ask you a quick question?"

"Sure." She said.

"I can guess what the food is for. You are probably on a strict diet or something, but what I don't get is why you needed 16 D size batteries."

Britney made this uncomfortable face. "If I tell you, do you promise that whatever I say doesn't leave this room?" I nodded. "Well, after a performance I get really wet and horny and usually fuck myself with a dildo."

I nodded, "Sounds like you need another boyfriend."

She nodded, "I haven't had sex with anyone since the one and only time with Justin." Again I nodded.

"Well,…um…Ms. Spears, that is er…I know I'm not the best looking guy in the world…but, if you wanna…you know…I wouldn't have a problem with…you know, doing it." I stuttered the entire way through because up to this point I was a straight up virgin.

Britney smiled, "So are you saying, if I wanted to fuck you, I'd tell you and we would." I gulped and nodded. She eyed me over. "From the way you're acting, I bet you're still a virgin?" I nodded. "And I'll bet you've never even seen a woman naked before you in person before?" Again I nodded. She smiled a wicked smile. "Well," She started, "I've always wanted to break in a virgin. Now take off your clothes." I didn't move a muscle. "Never been naked in front of a girl or anyone else either?" I nodded a very painful nod. "I'll step into the bathroom to freshen up a bit. When I come out I want to see a naked Errand Boy or else I'm going to be very pissed off." She went into the bathroom and in less than five seconds I was completely nude.

The door to the bathroom opened as I tried to cover myself but I had a problem. "What the fuck?" Britney whispered. You see I couldn't cover myself because I was very well endowed and it was very difficult to hide myself when I was at full attention. Britney walked over to me and gently pried my hands away. Her eyes widened and she said, "I've never seen one that size before." I reached my hand up and brushed against the corners of her mouth. "What was that for?" She asked.

"Sorry, but you had drool running down from the corners of your mouth." I even showed her the evidence.

"Sorry." She said. "You'd be the second guy I've been with and you make Justin look like a little kid. His dick was only five inches when it was fully erect. He couldn't satisfy a chicken to save his life. But you, you're a man. How old are you?" She asked.

"I just turned 18 two weeks ago." I replied.

"Hell, you make my vibrator look tiny and it's eight inches. And if I think right a virgin usually measures his cock, soo how big is that."

"Nine." I meekly replied. Britney pulled off her tight pink top and threw it aside, revealing a midnight blue bra underneath cupping those magnificent globes. She slid off the tight pair of blue pants to reveal a pink G-string underneath, protecting the pussy that men would kill just to see as is.

Britney took my hands in hers and put them behind her back and helped me unhook her bra. Next she moved our hands down and she helped me untie her G-string. We were now both naked. Britney then jogged over to the door and locked it to make sure we wouldn't be interrupted(her lovely breasts bounced the entire way, to and fro). She came back over to me and dropped to her knees, rubbing my cock and licking it. Being a virgin and all it didn't take long before I felt the need to cum. Roughly I pushed her away from me.

"What the fuck is that all about?" She said to me angrily.

"Sorry, but I was about to cum." I replied.

"So. What's the problem then?" She asked.

"I believe that a woman should always cum first, no matter what the circumstances." She smiled at hearing this. I went over to her and literally picked her up (I used to move stuff around before I was promoted to ‘Errand Boy', so I had some muscle even though it didn't appear that way). I gently placed her down onto the sofa and knelt down in front of her. She then spread her legs automatically and showed off her beautifully shaved pussy. I reached down and carefully pulled her pussy lips apart. The first thing that I noticed was her clit. It was silvery white and was about a half inch long.

"Looks like you're endowed yourself."

She smiled. "What do you mean."

"Well, I've read that a woman's clit averages about a quarter inch or so, yours has to be about a half inch." She blushed and her smile widened. I lowered my head and slowly licked her outer lips and gently massaged her mons with my free fingers.

Britney gave a soft moan. "For a virgin, you can handle a pussy pretty well."

"I've studied." Was my reply and I went back to work on my lips. I then released her outer lips and started to lick her inner lips while massaging her thighs. I then wet a finger with her juices and slid it down to her anus and lightly rubbed it around her ring.

Again she moaned. "Such a dirty Errand Boy you are." I smiled on the inside and pressed my finger gently into her asshole, slowly fucking her in and out with it. "Keep it up, I'm about to cum." She said. I moved my concentration up to her clit. I folded my tongue in half and slide her clit into the opening (almost as if her clit was a cock and my tongue was a pussy). I then started to slide my tongue up and down her clit while sucking and humming and fucking her ass faster and faster with my finger. Her juices flowed easily into my mouth. Her legs then wrapped around my head holding me there, her asshole tightened around my finger and she screamed out her orgasm.

"OH FUCK, FUCK, SHIT. KEEP GOING BABY. HOW DO YOU LIKE MY CUM FLOODING YOUR FACE YOU CUNT EATING MOTHER FUCKER!!!!" I just prayed that nobody heard us. Finally after a couple of minutes she loosened her legs as I swallowed her sweet ambrosia like liquid. I removed my finger from her ass and then moved my head down and started to lick up some stray liquid near her anus. Britney moaned out again.

"Enough of that for now. Justin didn't even do half as well. He licked my clit and as soon as I came he went to sleep while I masturbated to another orgasm. Hell, my finger felt better than his tongue. Now it's my turn she smiled." As we were switching positions we frenched while she licked her remaining cum from my face. I sat down on the couch and she slid between my legs. She licked her hand and slowly masturbated me getting me harder than ever. Next, she started to lick the sensitive purple head while massaging just under it. Then slowly she took my manhood into her mouth an inch at a time until she was at six.

"Take as much as you're comfortable with." She smiled around my cock and slide down to about eight inches where she stopped. I felt a strange tightness around my cock and awarded it to her deep-throating me. She bobbed furiously just letting her teeth scrape my cock. I told her I was about to cum and she started to suck me and masturbate me at the same time. Finally, I felt my balls let loose a torrent of cum. Moaning and groaning the first two spurts went down her throat, then she pulled my cock out of her mouth and the last seven squirts hit her in the face. She looked like she had been in one of them bukkake things. Cum dripped off her face. Britney took a finger and scooped it all into her mouth, moaning at the taste of it.

"God, I am so hot right now. Fuck me with that big powerful cock of yours." She got up and stood about me on the couch, her pussy practically in my face. I leaned forward and licked and drop off, making her giggle slightly. She slowly lowered herself onto my cock moaning every couple of inches until she was up to about six inches. "Damn." She said. "I need something to help me slide down some more." I looked around the room and the answer was right next to me.

"How about this Vaseline?" I asked.

She smiled. "That'll work." Quickly I spread the Vaseline onto the rest of my cock and Britney easily slid down the rest of the way. "Oh, shit. I feel so full and…" She stopped talking, her body froze, and she shook as her orgasm took her. She moaned softly until she was finished. "That felt so fucking good." She said smiling to me. "Tell me when you're gonna cum." I nodded. She started off at full blast, bouncing up and down on my cock. While I sucked, licked, and bit her nipples. She had two more orgasms before I felt the urge to cum.

"I'm gonna cum." I grunted out. She got off.

"Where do you want to cum?" I smiled.

"I want to cum in your ass." She looked shocked.

"I don't know if I can take it all."

"You don't have to. I'll go in as far as you can take it and then cum."

"Okay." She said uneasily, "Just tell me what to do."

"Bend over the couch." She did. I pulled her ass cheeks apart and started to eat her asshole out. When it was thoroughly wet I spread some Vaseline over it and greased my cock up. "Now just relax and this will be very easy and not very painful." I pushed my cock head against her asshole and pushed gently, the head slid in. Slowly I slid in inch after inch. She moaned and whimpered but never really said anything about being uncomfortable. Before I noticed it, I was all the way in to the hilt. I thrust into her twice before I held onto her and shot my load deep into her asshole. I pulled out and she fell onto the couch.

"That felt amazing." I just smiled and blushed. She got up off the couch and cleaned the remaining cum off my cock as some dripped out of her asshole. She then lay down on the floor. "Please don't tell me that you're one of those guys that hates to cuddle his girl after sex."

I smiled and leaned up against the couch and laid her down on my chest, softly stroking her hair and her breasts as she came down from her orgasmic pleasure. She looked up at me and smiled. Next time, I promise that you can cum in my pussy. By then I'll be on birth control.

"I'm sorry but you're not scheduled to appear her anymore this year." I said.

"Well," she said smiling, "I have a couple of days before my next concert so I had this idea." She said.

"What is it?" I asked.

"How would you like to come on tour with me and be my personal Errand Boy as well as my personal Fuck Boy."

I kissed her lips and as I nibbled her ear lobe and replied, "I'll tell my parents and pack tonight." She smiled at hearing this and gave me another kiss.

"I want to meet them, that away they'll know you're serious." About a half-hour later we were dressed and heading to my place in my car while her limo followed (after I told my boss about my new job). When I walked in, my parents were on the couch and I could have sworn that they nearly pissed their pants when Britney followed me in. We explained the situation and my parents gave me permission to go as soon as we were finished. I went into my room as Britney followed.

She saw my autograph collection and said, "Why didn't you ask me for one."

"I don't know." I replied. I took off my shirt and handed her a marker. She licked her lips but restrained herself as I started to toss a bunch of my clothes into my suitcase and duffel bag as she signed my shirt. She tapped me on the shoulder and said, "Where's your bathroom."

"Right across the hall." I pointed. She went in and came back out a couple of minutes later, closing my door when she entered.

I was packing up some notebooks when she said, "What are those?"

"Uh…just some uh…love poems that I have written."

I saw her smile, "Will you read some to me on the way to the hotel." I nodded. After I was totally packed I put on my polyester blue shirt with little samurai type men and Japanese writing on it and placed the now autographed yellow shirt in a frame. She then had me take a picture with her and I placed that in as well.

"Here." She said, "Put these in there as well. She handed me something pink, in fact it was her pink G-string that she had on earlier. I smiled and put it inside the shirt and hung up the shirt, picture, and G-string, I reached out and felt her pussy lips against the rough fabric of her blue jeans. I gave my parents a quick hug and kiss goodbye and tossed them the keys to my car, and we left in Britney's limo.

On the way to the hotel I whispered in her ear. "So how much do I get paid?"

She smiled again, "What did you make there at the music center?"

"Roughly 200 per event."

"How about I pay you 400 per concert? I may even have to give you a little bonus after each one." She gently rubbed my crotch. "Now how about you read me some of the poems you've written before we get to the hotel?" I pulled out a notebook and started to read while Britney snuggled up against me, rubbing her hand around my chest…